Fig 6 - uploaded by Stefan Schulz
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Determination of the absolute configuration of the macrocyclic lactone 3 from Hyperolius cinnamomeoventris by GC on a chiral Hydrodex β-6TBDM phase. A: (2S,10S)-3, B: (2R,10R)-3, C: (2S,10R)-3, D: (2R,10S)-3, E: natural lactone A, and F: coinjection of (2R,10S)-3 and natural lactone A. Strike through denotes impurities
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Frogs of the families Mantellinae and Hyperoliidae possess male specific femoral or gular glands that are used during courtship. These glands release volatile compounds, e. g. the macrocyclic lactone gephyromantolide A (2,6,10-trimethyl-6-undecen-11-olide) in the case of Gephyromantis boulengeri (Mantellinae). During the analysis of the volatiles o...
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Context 1
... stereoisomers in hand, the absolute configuration of the natural compound A was determined. This is important because chirality is a significant factor in the functionality of semiochemicals for species recognition (Mori 2007). For this purpose, the E/Z mixtures of all four stereoisomers were separated by GC on a chiral Hydrodex β-6TBDM phase (Fig. 6A-E). Since the peak of the (2R,5E,10S)-stereoisomer coincided with the naturally occurring lactone from H. cinnamomeoventris, a coinjection of the two samples was performed for confirmation (Fig. 6F). An intensification of the compound A peak was observed upon coinjection proved that the natural lactone is ...
Context 2
... species recognition (Mori 2007). For this purpose, the E/Z mixtures of all four stereoisomers were separated by GC on a chiral Hydrodex β-6TBDM phase (Fig. 6A-E). Since the peak of the (2R,5E,10S)-stereoisomer coincided with the naturally occurring lactone from H. cinnamomeoventris, a coinjection of the two samples was performed for confirmation (Fig. 6F). An intensification of the compound A peak was observed upon coinjection proved that the natural lactone is (2R,5E,10S)-2,6,10-trimethyl-5-undecen-11-olide. This compound proved to be a new natural product for which we propose the name cinnamomeoventrolide ((2R, ...
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Frogs of the families Mantellinae and Hyperoliidae possess male specific femoral or gular glands that are used during courtship. These glands release volatile compounds, e. g. the macrocyclic lactone gephyromantolide A (2,6,10-trimethyl-6-undecen-11-olide) in the case of Gephyromantis boulengeri (Mantellinae). During the analysis of the volatiles o...
Repurposing enzymes to catalyze non‐natural asymmetric transformations that are difficult to achieve using traditional chemical methods is of significant importance. Although radical C−O bond formation has emerged as a powerful approach for constructing oxygen‐containing compounds, controlling the stereochemistry poses a great challenge. Here we pr...
